As you may already know, not every user is able to get the most recent Windows 10 version right after its release. It usually takes quite long before it lands on all supported devices, due to Microsoft resolving compatibility issues with software and hardware, or just because of bugs in the OS. Many users are getting confused by not receiving the latest stable build, so Microsoft is about to make this process as transparent as possible.
Microsoft is now working closely with hardware and vendors to improve the upgrade experience. The company will use its artificial intelligence/machine learning tech to highlight potential problem areas before and after rollouts begin.
Another step Microsoft is taking is to better explain to users what is preventing their devices from getting the latest OS. While no real plans have been disclosed, Mary Jo Foley noted the following on ZDNet:
...Microsoft also is working to do what many Windows users have been requesting: Make blocking issues clearer and more customized. Microsoft's goal is to provide Windows 10 users with much more specific information on why their machines are blocked from receiving a particular update and to give them an inbox notification that is both specific and actionable, I hear. None of my contacts would say when something like this might happen, unfortunately, but at least it's on the list.
Windows 10 is designed to work on a variety of hardware, and the list of possible hardware combinations is actually huge. Due to this, Microsoft needs to perform more testing to resolve the issues before releasing a feature upgrade. Maybe by releasing new OS versions less frequently, e,g, one Windows 10 release per year as rumored earlier, the company will be able to handle the situation better.